Shelter Island Holidays from £1,116

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Your Shelter Island Holiday

Lock in a Shelter Island holiday package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighbourhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organising a tailored Shelter Island holiday is a cinch with Expedia.

Top Shelter Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Ridge Hotel
YOTEL New York Times Square
Hilton New York Times Square
The Plaza, A Fairmont Hotel
Seven Beach Lane

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island

Shelter Island Beach Holiday

There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
East Hampton Main Beach, Wolffer Estates Vineyard and 67 Steps Beach

Top hotels in Shelter Island

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is £499 per night from 17 May to 18 May
£499
17 May - 18 May
includes taxes & fees
8.4/10 Very Good! (779 reviews)
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!

Reviewed on 11 May 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is £153 per night from 18 May to 19 May
£153
18 May - 19 May
includes taxes & fees
9.2/10 Wonderful! (1,343 reviews)
Cute place great views would go back in the summer

Reviewed on 11 May 2026

Montauk Manor
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
The price is £296 per night from 21 May to 22 May
£296
21 May - 22 May
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Unhinged wacko

Reviewed on 6 May 2026

Montauk Yacht Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.